amyl nitrite
Nitrite Ion is a symmetric anion with equal N–O bond lengths. Nitrite is important in biochemistry as a source of the potent vasodilator nitric oxide. Nitrate or nitrite (ingested) under conditions that result in endogenous nitrosation has been classified as "Probably carcinogenic to humans" (Group 2A) by International Agency for Research on Cancer (IARC), the specialized cancer agency of the World Health Organization (WHO) of the United Nations. Sodium nitrite is used for the curing of meat because it prevents bacterial growth and, as it is a reducing agent (opposite of oxidation agent), in a reaction with the meat's myoglobin, gives the product a desirable pink-red "fresh" color, such as with corned beef. This use of nitrite goes back to the Middle Ages, and in the US has been formally used since 1925. Because of the relatively high toxicity of nitrite (the lethal dose in humans is about 22 milligrams per kilogram of body weight), the maximum allowed nitrite concentration in meat products is 200 ppm. At these levels, some 80 to 90% of the nitrite in the average U.S. diet is not from cured meat products, but from natural nitrite production from vegetable nitrate intake. Under certain conditions – especially during cooking – nitrites in meat can react with degradation products of amino acids, forming nitrosamines, which are known carcinogens. However, the role of nitrites (and to some extent nitrates) in preventing botulism by preventing C. botulinum endospores from germinating have prevented the complete removal of nitrites from cured meat, and indeed by definition in the U.S., meat cannot be labeled as "cured" without nitrite addition. They are considered irreplaceable in the prevention of botulinum poisoning from consumption of cured dry sausages by preventing spore germination. Nitrite is a member of the drug class antidotes and is used to treat Cyanide Poisoning. — NCATS
Clinical trial activity
6 trials · 8 clinical orgs · 0 marketing orgs
Earliest trial started Jan 1, 2010 (NCT01178359)
Timeline
Indications
Approved for
Mechanism of action
- Unspecified targetOTHER
Unknown
Amyl nitrite cause direct vasorelaxation through vascular generation of nitric oxide (NO) and relaxation via a cyclic guanosine monophosphate-dependent process.
Chemistry & pharmacology
SMILES
[O-]N=O- Mol. weight
- 46.0055 g/mol
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
Oral
No
Parenteral
No
Topical
No
Sources
- WikipediaNitrite ↗
- NCATSJ39976L608 ↗
- ChEMBLCHEMBL3833339 ↗
- WikipediaAmyl nitrite ↗
- NCATS22T8Z09XAK ↗
Also known as
- 1-nitropentane
- 1-nitropentane
- amylnitrit
- amyl nitrite
- amyl nitrite
- amyl nitrite
- amyl nitrite
- amyl nitrite
- amyl nitrite
- amyl nitrite
- amyl nitrite
- amyl nitrite
- n-amyl nitrite
- n-amyl nitrite
- nitramyl
- nitramyl
- nitramyl
- nitrite
- nitrite
- nitrite
- nitrite anion
- nitrite anion
- nitrite ion
- nitrite ion
- n-pentyl nitrite
- n-pentyl nitrite
- pentyl nitrite
- pentyl nitrite
- vaporole
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT04905173 | N/A | Nov 30, 2021 | Mayo Clinic |
| NCT02463357 | Phase 4 | Aug 1, 2015 | Alma College, University of Colorado, University of Colorado, Denver |
| NCT02428959 | N/A | Jun 1, 2014 | Johns Hopkins University |
| NCT01932606 | Phase 2 | Aug 1, 2013 | Mayo Clinic |
| NCT01431313 | Phase 2 | Apr 1, 2012 | University of Pittsburgh |
| NCT01178359 | Phase 1 | Jan 1, 2010 | Medic One Foundation, University of Washington |
Organizations
Research & Development (8)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Mayo Clinic | Academic/Hospital | 2 | 2 | 2 | 2013 |
| Alma College | Academic/Hospital | 1 | 0 | 1 | 2015 |
| Johns Hopkins University | Academic/Hospital | 1 | 1 | 1 | 2014 |
| Medic One Foundation | Academic/Hospital | 1 | 0 | 1 | 2010 |
| University of Colorado | Academic/Hospital | 1 | 0 | 1 | 2015 |
| University of Colorado, Denver | Academic/Hospital | 1 | 1 | 1 | 2015 |
| University of Pittsburgh | Academic/Hospital | 1 | 1 | 1 | 2012 |
| University of Washington | Academic/Hospital | 1 | 1 | 1 | 2010 |